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The Future of AI with Bret Taylor, Winston Weinberg, Garrett Lord and Aaron Holmes | Aug 20, 2025

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Aug 20, 2025
Bret Taylor, CEO of Sierra and OpenAI board chairman, and Winston Weinberg, co-founder of Harvey, dive into the rapidly evolving AI market. They spotlight advancements in AI agents, particularly in legal and customer service sectors. Garrett Lord from Handshake discusses how AI is reshaping job markets and the gig economy. Additionally, they tackle the paradox of rising costs in AI technologies and explore the financial implications for companies navigating this transformative landscape.
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INSIGHT

Best-Of-Breed Now, Platform Later

  • Demand for applied AI agents is extremely high because they deliver measurable business impact.
  • Best-of-breed startups win now, but platform consolidation may follow as the market matures.
ADVICE

Start With Narrow, Measurable Use Cases

  • Build domain-specific workflows and focus on narrow tasks to prove ROI quickly.
  • Use targeted automation (e.g., merger-control guidance) where outcomes are measurable and comparable to human labor.
INSIGHT

Sell Outcomes, Not Tokens

  • Applied AI vendors should sell business outcomes, not raw model usage or tokens.
  • Token costs matter less when your product meaningfully reduces customer costs or increases revenue.
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